Title: The Best Hotels in Oakland, Chicago - 2025 Updated Prices | Expedia.co.uk [Holiday Rentals in Chicago](https://expedia.co.uk/Chicago-Holiday-Rentals.d178248.Travel-Guide-HolidayRentals)[Flights to Chicago](https://expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.co.uk/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Oakland Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Oakland.d6132392.Car-Hire-Guide)[Oakland Holidays](https://expedia.co.uk/Oakland.d6132392.Holidays-City-Breaks) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Hotels in Oakland, Chicago ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Oakland Spa [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&amenities=SPA_ON_SITE) Pet friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&amenities=PETS) Family friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&travelerType=family_friendly) Apart hotel [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&lodging=APART_HOTEL) Condo [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&lodging=CONDO) Waterpark [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&amenities=WATER_PARK) Hot tub [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&amenities=HOT_TUB) Apart­ment [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&lodging=APARTMENT) Pool [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&amenities=POOL) Cottage [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&lodging=COTTAGE) ## Check prices for these dates Tonight [10 Oct - 11 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6132392&startDate=2025-10-10&endDate=2025-10-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [11 Oct - 12 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6132392&startDate=2025-10-11&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [10 Oct - 12 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6132392&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [17 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6132392&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Property class ## Top Trending Hotels Near Oakland, Chicago ![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/7697ff8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception hall](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/edcb7f57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eurostars Magnificent Mile River North, 5 mi from Oakland 9.0/10 Wonderful (3071) "The hotel has a restaurant on the first floor with patio seating and great views." £95 includes taxes & fees 10 Nov - 11 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![Cocktail bar](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/ada94c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, free cots/infant beds, free WiFi](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/50be090a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Chicago Mag Mile Streeterville, 4.9 mi from Oakland 8.6/10 Excellent (2855) "Had a great stay!" £122 includes taxes & fees 9 Nov - 10 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![Outdoor pool, pool cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b1113923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/8e39b688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b131add8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Chicago - Magnificent Mile Streeterville, 4.8 mi from Oakland 8.8/10 Excellent (2084) "Great hotel" £139 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e85c42c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e50ef89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Single Beds | Premium bedding, desk, laptop workspace, free WiFi](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/6d4883c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Hotel The Loop, 4.6 mi from Oakland 8.8/10 Excellent (4732) "Staff friendly and helpful..and accommodations just right..great location! " £97 includes taxes & fees 9 Nov - 10 Nov [](https://www.expedia.co.uk/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/2866aa1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/5d460cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/55a8ba7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Streeterville, 4.7 mi from Oakland 9.4/10 Exceptional (2180) "Great hotel " £166 includes taxes & fees 10 Nov - 11 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/c14e1876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/cb4330d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/2aaf07f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Freehand Chicago River North, 4.9 mi from Oakland 8.0/10 Very good (2442) "Great place" £76 includes taxes & fees 10 Nov - 11 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, City View | Living area | TV](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/cc919354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Suite, 1 King Bed, Lake View, Lakeside | Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e932b9a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Congress Plaza Hotel The Loop, 3.7 mi from Oakland 8.0/10 Very good (9366) "Beautiful hotel!" £113 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/b9be2277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/18c5ca41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/59baefbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile River North, 4.9 mi from Oakland 8.4/10 Very good (4059) "We definitely will stay there again place was very nice " £148 includes taxes & fees 30 Oct - 31 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/1792d463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/bb272e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, City View | View from room](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/c06f4b61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### citizenM Chicago Downtown Theatre District, 4.5 mi from Oakland 9.2/10 Wonderful (3929) "Great place to stay. " £123 includes taxes & fees 10 Nov - 11 Nov [](https://www.expedia.co.uk/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information) ![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/07c9ead9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/d24507d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/0030a761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago/Magnificent Mile Suites Streeterville, 5.3 mi from Oakland 8.8/10 Excellent (3063) "Our stay was great" £126 includes taxes & fees 9 Nov - 10 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed | Living area | 37-inch TV with cable channels, pay films](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b812d0f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b5bf3aa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/bbeef356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago The Loop, 3.6 mi from Oakland 8.4/10 Very good (2252) "We loved this hotel it was beautiful and convenient . " £184 includes taxes & fees 23 Oct - 24 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/f7f78ace.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/f9eed5f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/520a670b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 2 Double Beds, Non Smoking, Refrigerator (with Sofabed) | 1 bedroom, pillow-top beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/aeb6fede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western River North Hotel River North, 5 mi from Oakland 7.8/10 Good (1021) "Great stay" £89 includes taxes & fees 9 Nov - 10 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Best-Western-River-North-Hotel.h17227.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/cbeee5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/68145d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/2b6118c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/9ab0dcf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### FOUND Hotel Chicago River North River North, 5 mi from Oakland 8.2/10 Very good (271) "Perfect location! Tons of restaurants and shopping nearby! " £75 includes taxes & fees 9 Nov - 10 Nov [](https://www.expedia.co.uk/Chicago-Hotels-FOUND-Hotel-Chicago.h113779814.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/cc779b7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 King Bed with Sofa bed | 1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/f5c52beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/c0ded825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Riu Plaza Chicago Streeterville, 4.9 mi from Oakland 9.4/10 Exceptional (2576) "Great place to stay " £151 includes taxes & fees 9 Nov - 10 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ![American cuisine](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast for a fee](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/c46ad167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/5b3c70b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![American cuisine](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/fb80c7da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Crowne Plaza Chicago West Loop by IHG 4.6 mi from Oakland 9.0/10 Wonderful (1584) "Excellent breakfast and room was quiet and clean. " £114 includes taxes & fees 9 Nov - 10 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/6b27f192.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, free cots/infant beds](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/64c4029a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/dd081548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/5496cb17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### voco Chicago Downtown - Riverwalk by IHG River North, 4.8 mi from Oakland 8.8/10 Excellent (3198) "Great stay " £141 includes taxes & fees 9 Nov - 10 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2510000/2506500/2506471/b573f792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2510000/2506500/2506471/d5770f58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2510000/2506500/2506471/891da469.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, iron/ironing board, free cots/infant beds](https://images.trvl-media.com/lodging/3000000/2510000/2506500/2506471/0aef82d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Chicago Downtown The Loop, 4.3 mi from Oakland 8.6/10 Excellent (2572) "Good place to stay" £140 includes taxes & fees 9 Nov - 10 Nov [](https://www.expedia.co.uk/Chicago-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Chicago-Downtown.h2506471.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/af0ef9e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/c12c78f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/0ec157ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/w3576h2561x0y0-5f9110d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric The Loop Chicago Theatre District, 4.2 mi from Oakland 9.0/10 Wonderful (2174) "It was an amazing stay!" £160 includes taxes & fees 9 Nov - 10 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Hyatt-Centric-The-Loop-Chicago.h9069667.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/197000/196959/b675990c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, laptop workspace, free cots/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/200000/197000/196959/0bc5a1e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/200000/197000/196959/d94e8d8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, laptop workspace, free cots/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/200000/197000/196959/1daf4199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Downtown Chicago The Loop, 3.7 mi from Oakland 7.4/10 Good (2402) "Comfortable bed, bright room, good shower, very accessible location." £89 includes taxes & fees 10 Nov - 11 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Travelodge-By-Wyndham-Downtown-Chicago.h196959.Hotel-Information) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/8318473d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/01c93cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palmer House a Hilton Hotel Theatre District, 4.1 mi from Oakland 8.4/10 Very good (2003) "Great place to stay." £179 includes taxes & fees 30 Oct - 31 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.co.uk/Hotel-Search?startDate=2025-10-24&endDate=2025-10-25®ionId=6132392&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FOakland-Chicago-Hotels.0-n6132392-0.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOakland-Chicago-Hotels.0-n6132392-0.Travel-Guide-Filter-Hotels) ## Where to stay in Oakland Find the best Oakland areas for the activities you enjoy most. - Downtown Chicago - Magnificent Mile - The Loop - River North - Lincoln Park ![Downtown Chicago featuring a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332072-Downtown-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191755-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Downtown Chicago showing a high-rise building and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332087-Downtown-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Downtown Chicago which includes signage](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332073-Downtown-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Downtown Chicago which includes signage and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332084-Downtown-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.co.uk/Hotel-Search?pwaOverlay=map®ionId=6350699) ![Downtown Chicago map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:uxq%7EFvjavOurAq%40mA%7DgDuTtO%7BFzJuOr%40mk%40z_%40MifBum%40%7EAGmaAx%7EAopCna%40uM%7EoC%7C%7DAx%40%7CkCnk%40yAy%40n%7B%40gt%40dE%7Bg%40pFo%40%60%7EB&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=XpzTv33-iXOpq3icViGLtz3e_jE=) ### Downtown Chicago The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art. [See properties](https://www.expedia.co.uk/Hotel-Search?regionId=6350699) ![Magnificent Mile - River North](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24577-Magnificent-Mile.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543374-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Magnificent Mile - River North which includes signage and heritage architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191832-Magnificent-Mile.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Magnificent Mile - River North showing street scenes as well as a large group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191836-Magnificent-Mile.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Magnificent Mile - River North which includes a city, a hotel and skyline](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24572-Magnificent-Mile.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.co.uk/Hotel-Search?pwaOverlay=map®ionId=800025) ![Magnificent Mile map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:gnt%7EF%60dyuOugAK%3FcChgALJ%60C&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=eJaOW3wrdH9kguwKvLeM9_7UbMs=) ### Magnificent Mile Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes. [See properties](https://www.expedia.co.uk/Hotel-Search?regionId=800025) ![The Loop - Downtown featuring a river or creek](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192013-The-Loop-Downtown.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543387-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543370-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![The Loop - Downtown showing a ferry and a river or creek](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191752-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192010-The-Loop-Downtown.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.co.uk/Hotel-Search?pwaOverlay=map®ionId=800024) ![The Loop map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:syr%7EFxx%7BuOqa%40mAeEqK_%40sp%40kG%7BKvAwg%40Xok%40%7C_%40x%40xF%7EPtlAi%40dCh%40DzOxDxCDnbBkNr%40e%5E%7EEkKzGiVfC&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=XwfHKgKFqor-NvwNZdw8nZOnNbI=) ### The Loop Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean. [See properties](https://www.expedia.co.uk/Hotel-Search?regionId=800024) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543369-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543384-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Shops at North Bridge featuring street scenes, cbd and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191962-Shops-At-North-Bridge.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191756-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Shops at North Bridge which includes central business district, street scenes and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191961-Shops-At-North-Bridge.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.co.uk/Hotel-Search?pwaOverlay=map®ionId=6350695) ![River North map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:%7B%7Cu%7EFl_%7DuOWcpA%7CECQ%7Db%40xi%40w%40nGbNJ%7Ep%40xCbHxAdBcB%7ECuAhA%7DKdCyGvFiGdDsD%7CDeCzEwBfBoN%5E&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=pVk_WdkeHd9iD-9kitVtoqcFN2A=) ### River North Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city. [See properties](https://www.expedia.co.uk/Hotel-Search?regionId=6350695) ![Chicago featuring a city and modern architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54398-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24578-Chicago-History-Museum.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Lincoln Park Zoo featuring autumn leaves and signage](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26661-Lincoln-Park-Zoo.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24579-Chicago-History-Museum.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Chicago History Museum showing interior views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24583-Chicago-History-Museum.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.co.uk/Hotel-Search?pwaOverlay=map®ionId=6059328) ![Lincoln Park map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:u%7E%7C%7EFhscvO%40%7DMjAWEyE_JFsDaCAl%40qDD%3F%7DBjU_%40AkAiAQ%40aWbAKAyFqALQeJzAIKaNiAJOgUTi%40%7E%40KEgF_BD%3FuMbBMc%40_NiAAI%7DImAIKmB%7CAQMeVxAKQ%7BOwGaCnCQHeCtBKFgC%7DAUSaGbBIx%40i%60Axp%40mMbD%7EGpa%40%7DJpR%7DM%60NgVzGrLV%60n%40mJ%7EEh%40%60AfIKClIuCNp%40xRrBWl%40b%7EAoEJoElF%7CArEjIiGKpNoVzJqItQvCfKsArA%7DL%60FuXhVm%40%60NaKhR%7BK%7CAcFbKiAzFsK_MqLbN%7DAJ&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=KktfaLNeQ_9ZFVphttKdls3N5TA=) ### Lincoln Park Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining. [See properties](https://www.expedia.co.uk/Hotel-Search?regionId=6059328) ## Top Oakland Hotel Reviews ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Great stay" [](https://expedia.co.uk/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![InterContinental Chicago Magnificent Mile by IHG](//images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg) ### InterContinental Chicago Magnificent Mile by IHG 10/10 Excellent "-" [](https://expedia.co.uk/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ![Hilton Garden Inn Chicago Downtown/Magnificent Mile](//images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8_y.jpg) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile 10/10 Excellent "good location. short walk away to many attractions" [](https://expedia.co.uk/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) ![citizenM Chicago Downtown](//images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd_y.jpg) ### citizenM Chicago Downtown 10/10 Excellent "Guest services on location was wonderful!!" [](https://expedia.co.uk/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information) ![The Wade](//images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg) ### The Wade 10/10 Excellent "Right across the street from the navy pier! Everything about the hotel is amazing as far as the lobby, weight room, pool, and room. The only thing that wasn’t good was the beds themselves. The weren’t comfortable. Other than that great place to stay." [](https://expedia.co.uk/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg) ### The Allegro Royal Sonesta Hotel Chicago Loop 10/10 Excellent "Very friendly staff. Great at deco decor. " [](https://expedia.co.uk/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Awesome hotel. Super nice staff!" [](https://expedia.co.uk/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "Excellent location, clean and good room partners " [](https://expedia.co.uk/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Sable at Navy Pier Chicago, Curio Collection by Hilton](//images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg) ### Sable at Navy Pier Chicago, Curio Collection by Hilton 10/10 Excellent "Everything was wonderful. The lil shopping and big variety of the food was so close. You didn’t have to go off the Pierre to do anything really unless you wanted to do some big shopping the view of the hotel was magnificent as the Chicago and I will come back here as many times as I can such a great stay" [](https://expedia.co.uk/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Oakland that travellers recommend? > [Sophy Hyde Park](https://www.expedia.co.uk/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information) is a standout hotel located in the vibrant city of Chicago, boasting an exceptional score of 9.6. Guests appreciate its blend of modern luxury and historical charm, with high-end amenities such as premium bedding, customized bathrobes, and a stunning terrace great for relaxation. The hotel's prime location in the Historical District allows easy access to local attractions, making it an ideal choice for couples seeking a romantic getaway or travellers looking to explore the city's rich culture. > > > > For families, the [Hyatt Place Chicago-South/University Medical Center](https://www.expedia.co.uk/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) shines with a rating of 8.8. Its spacious rooms feature sofa beds and cribs, ensuring comfort for all ages. The hotel offers a complimentary buffet breakfast, making mornings straightforward. Kids will love the indoor pool, while parents can enjoy the 24-hour fitness facilities. The family-friendly atmosphere is enhanced by the option for kids' meals, allowing everyone to dine happily together. ### What hotels in Oakland offer free breakfast? > [Hyatt Place Chicago-South/University Medical Center](https://www.expedia.co.uk/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) is a fantastic option for families visiting Chicago. Rated 8.8 by guests, this hotel offers a complimentary buffet breakfast, ensuring that everyone starts the day off right. With an indoor pool, kids can splash around while parents unwind, making it a great spot for family fun. ### What are the best budget hotels in Oakland? > [Hyatt Place Chicago-South/University Medical Center](https://www.expedia.co.uk/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) is an excellent budget-friendly option for families visiting Chicago. This hotel boasts a spacious indoor pool, which is great for kids to splash around while parents relax nearby. Guests appreciate the complimentary breakfast, featuring a delightful buffet that caters to various tastes, ensuring the whole family starts their day right. ### What are the most romantic hotels in Oakland for couples? > For couples seeking a romantic getaway in Oakland, [Sophy Hyde Park](https://www.expedia.co.uk/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information) is an exceptional choice, boasting a stellar rating of 9.6. This hotel is situated in a charming historical district, enveloping guests in a special environment that melds history with modern comforts. ### Can I cancel my hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Oakland hotel for you. ### How can I save on a Oakland hotel booking with Expedia? > Before booking your Oakland hotel, remember to join Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. You could also enjoy savings by bundling together your hotel and flights on Expedia. ### How much is the nightly rate at a Oakland hotel? > Hotel prices in Oakland often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates. ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - Other - More ways to book - [4 Star Hotels in McKinley Park](https://www.expedia.co.uk/4Star-McKinley-Park-Chicago-Hotels.s40-n6132389-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in New City](https://www.expedia.co.uk/5Star-New-City-Chicago-Hotels.s50-n6132388-0.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Armour Square](https://www.expedia.co.uk/Armour-Square-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132365-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Bridgeport Hotels](https://www.expedia.co.uk/Bridgeport-Chicago-Hotels.0-n6132075-0.Travel-Guide-Filter-Hotels) - [Bronzeville Hotels](https://www.expedia.co.uk/Bronzeville-Chicago-Hotels.0-n6132245-0.Travel-Guide-Filter-Hotels) - [Canaryville Hotels](https://www.expedia.co.uk/Canaryville-Chicago-Hotels.0-n6132307-0.Travel-Guide-Filter-Hotels) - 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